1. Field of the Invention
This invention relates to bis-naphthalimides, processes for their preparation, pharmaceutical compositions containing them, and methods of using them to treat cancer in mammals.
2. Prior Art
Harnisch, et al. in U.S. Pat. No. 4,841,052 issued June 20, 1989 describe naphthalic acid imides of the formula ##STR1## wherein: A.sup.1 represents C.sub.2 -C.sub.5 alkylene;
K.sup.1+ represents ##STR2## R.sup.6 represents C.sub.1 -C.sub.16 alkyl, carbamoylmethyl or benzyl; R.sup.7 represents methyl or ethyl or a single bond linked to D; PA1 R.sup.8 represents methyl or ethyl; PA1 W.sup.1 represents ##STR3## Z.sup.1 represents --CH.sub.2 --, or ##STR4## --O-- or --SO.sub.2 --; and X represents an unsubstituted benzosulphonate or a benzenesulphonate substituted by chlorine or C.sub.1 -C.sub.12 alkyl, a C.sub.5 -C.sub.18 alkylsulphonate or a salt of a C.sub.5 -C.sub.18 alkylcarboxylic acid or a salt of a condensation product of formaldehyde and arylsulphonic acids and/or optionally sulphonated 4,4'-dihydroxydiphenylsulphone, wherein D represents --CH.sub.2 --, --CH.sub.2 --CO--, --CH.sub.2 --CO--HN13 or --CH.sub.2 --CO--NH--CH.sub.2 -- and m represents 0 or 1. PA1 R, R' and R.sup.1 independently are H, C.sub.1 -C.sub.6 alkyl, benzyl optionally substituted with 1 or more substituents independently selected from the group consisting of: PA1 R.sup.2, R.sup.5 and R.sup.7 independently are H or C.sub.1 -C.sub.3 alkyl including cyclopropyl; PA1 R.sup.3 and R.sup.4 independently are H or C.sub.1 -C.sub.6 alkyl; PA1 R.sup.6 and R.sup.8 independently are C.sub.1 -C.sub.6 alkyl; PA1 X, X', Y and Y' independently are selected from the group consisting of: PA1 R.sup.9 and R.sup.10 independently are H or C.sub.1 -C.sub.6 alkyl; PA1 each .alpha. is independently a single or a double bond; and PA1 m and p independently are 2-10. PA1 A is RN(CH.sub.2).sub.n NR'; and/or PA1 R and R' are C.sub.1 -C.sub.6 alkyl; and/or PA1 n is 2-6; and/or PA1 m and p independently are 2-6; and/or PA1 X, X', Y and Y' are H; and/or PA1 each .alpha. is a single bond. PA1 (a) 1,4-Bis-[3-(1,3,6,7-tetrahydro-1,3-dioxo-2H-indeno[6,7,1-def]isoquinoline- 2-yl)propylamino]butane, or the dihydromethane sulfonate salt or dihydrochloride salt thereof. PA1 (b) 1,4-Bis[3-(1,3,6,7-tetrahydro-1,3-dioxo-2H-indeno[6,7,1-def]isoquinoline-2 -yl)-N-ethylpropylamino]butane, or the dihydrochloride salt thereof. PA1 (c) 4-[3-(1,3,6,7-tetrahydro-1,3-dioxo-2H-indeno[6,7,1-def]isoquinoline-2-yl)p ropylamino]-1-(1,3,6,7-tetrahydro-1,3-dioxo-2H-indeno-[6,7,1-def]isoquinoli ne-2-yl)butane, or the methanesulfonate salt thereof.
These compounds are highly suitable as charge-regulating substances in electrophotographic toners.
U.S. Pat. No. 4,874,863 issued Oct. 17, 1989 discloses compounds of the Formula (I) ##STR5## wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are identical or different and are each H, NO.sub.2, NH.sub.2, C.sub.1 -C.sub.6 alkylamino, di-C.sub.1 -C.sub.6 alkylamino, OH, C.sub.1 -C.sub.6 alkoxy, halogen, trihalomethyl, C.sub.1 -C.sub.6 alkyl, formyl, C.sub.1 -C.sub.6 alkylcarbonyl, ureyl, C.sub.1 -C.sub.6 alkylureyl and R is a straight chain or branched C.sub.4 -C.sub.10 alkylene which is interrupted at one or two points in the chain by a secondary or tertiary amino group, where 2 nitrogen atoms may additionally be bonded to one another by an alkylene group, or a salt with a physiologically tolerated acid.